MedKoo Cat#: 574892 | Name: Taurolidine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Taurolidine is a synthetic taurine analog with antimicrobial and anti-neoplastic actions. Taurolidine and its metabolites mimic mannose by binding to the extracellular wall of bacteria, blocking adherence to epithelial and fibroblast cells. In addition to modulating immunoregulatory systems, taurolidine induces autophagy, apoptosis, and necrosis in human cancer cells. It produces cell death in malignant mesothelioma cells by oxidative stress in concert with inhibition of Akt signaling.

Chemical Structure

Taurolidine
Taurolidine
CAS#19388-87-5

Theoretical Analysis

MedKoo Cat#: 574892

Name: Taurolidine

CAS#: 19388-87-5

Chemical Formula: C7H16N4O4S2

Exact Mass: 284.0613

Molecular Weight: 284.35

Elemental Analysis: C, 29.57; H, 5.67; N, 19.70; O, 22.51; S, 22.55

Price and Availability

Size Price Availability Quantity
5mg USD 205.00 2 Weeks
10mg USD 335.00 2 Weeks
25mg USD 545.00 2 Weeks
50mg USD 800.00 2 Weeks
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Related CAS #
No Data
Synonym
Taurolidine
IUPAC/Chemical Name
4,4'-methylenebis(1,2,4-thiadiazinane 1,1-dioxide)
InChi Key
AJKIRUJIDFJUKJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H16N4O4S2/c12-16(13)3-1-10(5-8-16)7-11-2-4-17(14,15)9-6-11/h8-9H,1-7H2
SMILES Code
O=S1(CCN(CN2CNS(CC2)(=O)=O)CN1)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 284.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1. Calabresi, P., Goulette, F.A., and Darnowski, J.W. Taurolidine: Cytotoxic and mechanistic evaluation of a novel antineoplastic agent. Cancer Research 61(18), 6816-6821 (2001). 2. Caruso, F., Darnowski, J.W., Opazo, C., et al. Taurolidine antiadhesive properties on interaction with E. coli; its transformation in biological environment and interaction with bacteria cell wall. PLoS One 5(1), e8927 (2010). 3. Watson, R.W., Redmond, H.P., McCarthy, J., et al. Taurolidine, an antilipopolysaccharide agent, has immunoregulatory properties that are mediated by the amino acid taurine. Journal of Leukocyte Biology 58(3), 299-306 (1995). 4. Chromik, A.M., Daigeler, A., Bulut, D., et al. Comparative analysis of cell death induction by taurolidine in different malignant human cancer cell lines. J.Exp.Clin.Cancer Res. 29, 21 (2010). 5. Stendel, R., Biefer, H.R., Dékány, G.M., et al. The antibacterial substance taurolidine exhibits anti-neoplastic action based on a mixed type of programmed cell death. Autophagy 5(2), 194-210 (2009). 6. Aceto, N., Bertino, P., Barbone, D., et al. Taurolidine and oxidative stress: A rationale for local treatment of mesothelioma. European Respiratory Journal 34(6), 1399-1407 (2009).